Access to Ring-Expanded Analogues of 2-Amino Sugars

作者:Saha Jaideep; Peczuh Mark W*
来源:Organic Letters, 2009, 11(19): 4482-4484.
DOI:10.1021/ol9018387

摘要

Ring-expanded 2-N-acetylamino sugar analogs Of D-glucose, D-galactose, and D-mannose have been prepared by a new synthetic route. Aspects of the highly substituted (x-amino aldehyde intermediates made them central to the approach, First, they were accessed via diastereoselective addition of a vinyl Grignard onto protected glycosyl amines. Also, the sterics of the bis-protected amine favored the formation of only one glycoside anomer. The new analogues reported here should prove useful in the development of tools to investigate the role of 2-amino sugars in biology.

  • 出版日期2009-10-1